His father, Eddie Heyward, Sr. was also a jazz musician from the 1920s and provided him with training from the age of 12 as an accompanist playing in the pit band in a vaudeville theater in Atlanta, occasionally accompanying singers such as Bessie Smith and Ethel Waters. Heywood moved, first to New Orleans and then to Kansas City, when vaudeville began to be replaced by sound pictures.[1] Heywood played with several popular jazz musicians such as Wayman Carver in 1932, Clarence Love from 1934 to 1937 and Benny Carter, who heard him in Kansas City playing with Clarence Love, from 1939 to 1940 after moving to New York in 1938.[2]

Then, in 1947, Heywood was stricken with a partial paralysis of his hands and could not play at all.[2] However, it did not stop him when he made a comeback in 1951. In the 1950s, Heywood composed and recorded "Land of Dreams" and "Soft Summer Breeze" (which peaked at number 11 on the Billboard chart). He is probably best known for his 1956 recording of his composition "Canadian Sunset" (which peaked at number 2) which he recorded with Hugo Winterhalter and his orchestra for RCA Victor. After a second partial paralysis from 1966 to 1969, Heywood made another comeback and continued his career into the 1980s.[2]

Heywood died at home in Miami, Florida, aged 73. Parkinson's disease had been complicated by Alzheimer's disease, and Heywood had been in poor health for five years.[1]